Of Blair Bass and Chuck Waldorf
by AssKickinBitch
Summary: She's Blair Cornelia Bass,the ultimate princess of the Upper East Side. He's Charles Bartholomew Waldorf, his father's gay.
1. Chapter 1

**A/N: Kinda starts off as 1x07. Just had a thought about the reciprocation, but let's see where it goes.^^**

* * *

**Of Blair Bass and Chuck Waldorf**

She's Blair Cornelia Bass, the only daughter of NY C's business tycoon Bart Bass, making her the ultimate princess of the Upper East Side.

He's Charles Bartholomew Waldorf, the infamous son of fashion designer Eleanor, and chef Harold Waldorf, known for his nickname Chuck and being a certified Casanova.

When these two come together, what would become of the Upper East Side?

* * *

**Chapter One**

"OUT! YOU SLUTS!"

Eleanor Waldorf pulled two blonds out of the door and shut it. She tried to compose herself, seeing his son put on his boxers with a yawn. It's been the third time this week that she has caught Chuck naked in bed, feasting on two dames each time she did.

"You could've at least knocked." Chuck said, sitting on his bed.

"Well, you should learn to keep your clothes on." She commented.

"Why do you care so much?"

"Because."

He rolled his eyes and covered himself with his sheets.

"Nate's here."

"Oh." Chuck got up, and a folder on his desk caught his eyes. "Before I forget, mother, I have a proposal."

"Business?"

"Purely."

"Are you sick?" Eleanor leaned closer. "Charles, this is stunning."

"Oh, you bet." He smiled. "I found this place a couple of weeks ago and it sells itself. Literally."

"I'll let George have a look at it later. Okay?"

"Okay is great."

*

Blair stared at the wall clock in front of her. It's been twenty minutes since she called for breakfast, but her father, Bart Bass was still out of sight. She had told the kitchen staff to prepare Old English food since her father is going away to Asia for a business and won't be back for a few weeks. Dorota had been going in and out of the room, trying to see if Mr. Bass will be coming.

"Miss Blair." she said, escorting a hotel staff who held a letter in his hands.

"From Mr. Bass, Miss Blair." The staff handed her the letter.

"Thank you" she said, opening it and began reading to herself.

**_Blair,_**

**_I'm in California. _**

**_See you with the Archibalds at dinner._**

**_Behave, okay?_**

It wasn't even his handwriting. He just e-mailed it minutes ago and had the staff printed it. Was it that hard to personally right a good-bye letter or even to call his own daughter?

"Miss Blair." Dorota looked worried.

"It's okay D." She set aside the letter. "Just join me for breakfast."

"What about me?" a new voice contributed.

"S." Blair's face lit up. "I thought you had something coming up today."

"It's Sunday B. I wouldn't want to miss our Audrey sessions." Serena said. "And I brought Lady Godiva with me."

They hugged each other and squeaked in laughter. The only thing to make Blair Bass feel better is a few hours with her best friend. A sad fact about our princess is that she has everything-a wonderful best friend, gorgeous Nate Archibald for a boyfriend, the Palace for a home, designer dresses and shoes and everything-everything except her father.

He hasn't been spending much time with her since childhood. Her mother died when she was born, leading to actually blame herself for her mother's death. Even on holidays, when Bart was away, he would just send her gifts and a greeting card without the words Blair wanted to hear. She tried everything she thought that would make him proud of her. She had unblemished A's at school, she was never in detention, and she tried to look her bestest whenever they attended parties that pressed the need for him to introduce her to his business partners.

She even stayed away from the distractions Nate could bring. She wasn't entirely needing it at the moment, she just wanted to look perfect for her father, that maybe the next time he sees her, she'd see her as his daughter.

*

"I saw blonds and heard Eleanor screaming back there." Nate said.

"Ah.. the usual." Chuck took a hit from his joint. "You shouldn't be surprised, Nathaniel."

"What does your dad say?"

"Should he say something? He's in Paris getting laid with his Ro-Man. He doesn't care."

Nate sighed, slapping his best friends back. Chuck just found out about his father being gay. He has never talked to him after knowing it. He didn't even come to his father off. After all this years, Harold has been his hero. All those basketball games, all those car races they've seen, all those talk about girls and their pleasures, all those father and son bondings felt phony to Chuck. He'd been hurt, especially that his father was the only man he trusted, aside from Nate.

It was because he never felt that Eleanor loves him. She's been terrible to him, always seeing that something's wrong about him. Chuck felt that to her, he was a tangled thread in a fabric that she'd just dispose if she can't untangle it. But there was Harold, always there to see him eat breakfast, always there to lecture him about STDs, making him feel that everything's okay.

But he's not here now. And Chuck felt wasted.

Nate on the other hand has been thinking about the family dinner with Blair this evening. Captain has been quite exited since he had a business proposal with Bart that needs the tycoons signature. But the young Archibald was bothered. Stick to the plan and stick with Blair? or Stop and get a life he wanted? He took out the Cornelius Van der Bilt ring his mother wanted to give Blair and Chuck saw it in an instant.

"So, you proposing?" He scoffed. "Not that I object Nathaniel. But isn't it too early? You've been together since kindergarten, though."

"What do you suggest?" Nate sighed. "My parents think I should. I mean, I do love Blair, and..."

"The question is, do you want to?"

He remained silent.

"Anyway," Chuck continued. "I'll be opening my bar this evening. You up for it?"

"I have dinner with Blair." Nate said. "After may be."

"I'll send a car."

*

**Later that afternoon...**

Chuck sat on the couch at a the place he wanted Eleanor to invest at with a girl on his lap, eating cherries. School was a bummer and he decided to ditch Local History for burlesque dancers.

"I knew this was all foolishness." Eleanore appeared.

"Mom." Chuck pushed the dancer away from him. "I thought George-"

"George is absent." She snorted. "And I came here because I saw how eager you were. But I was wrong. And aren't you supposed to be at school?"

Chuck rolled his eyes.

"When are you going to grow up?" His mother strolled to the exit.

He wanted this place so badly. Not because of the girls and drinks. But because he knew this could bring profit for him. Plan A didn't work. Time for Plan B.

*

The Captain and young Archibald were inside one of the Upper East Side restaurants taking lunch. Or was it just?

"You have to do this now." His dad pushed.

"Dad. This is absurd." Nate whispered. "I don't wanna hurt Blair anymore."

"Hurt her?" He scoffed. "With this, she'll be happy! I know!."

"No, you don't know! I'm in love with someone else."

"That someone else is not worth it! This is Blair Bass. Don't you understand?"

**That night…**

Nate have been waiting by the stairs, quite nervous of what was to happen that night. Anything could happen-he might propose, he might run away. Still, he was thankful for Jenny for not telling Blair a word of what he did at the masquerade. Finally, she descended, wearing her silver dress. He gulped and took a deep breath.

"Hey." He said.

"Hey." Blair leaned to kiss him, but he drew back. .She was stunned, but it wasn't that visible in her expression.

"I don't see your father." Nate noticed.

"He'll be home soon."

She joined them in the living room where the Captain was having a drink already. Bart arrived moments later and apologized for the delay.

"We understand, Bart." He said. "Schedules and all are busy. Well, now that we're all here, shall we start?"

Bart sat beside his daughter and whispered; "The dress doesn't look good."

Blair clutched her ribbon and gulped. "I'm sorry dad."

"Don't you have anything to say, Nate?" Anne asked.

They all looked at him, and Blair was certain the time was now. Finally, her prince charming is going to ask for her hand.

"Well. Blair and I," He began. "Have been long friends. And I certainly am lucky to have been loved by her."

She smiled at him, that should've made him happy, instead he felt like a liar.

"I want all of you to know, that, Blair, I…"

A beep. Both their phones received a message, and a picture of the captain and Nate's quarrel at lunch.

**_Spotted: Archibald father and son having what it seemed like a fight over lunch. What were they arguing about? I'm pretty sure Queen Bee wants to know this now. Why don't you tell her yourself N? before you hand her your engagement ring_**

"Nate?" Blair looked at him.

He gave a quick look at his dad and walked out.

"Nate!" Blair ran after him.

She found him almost boarding a limosine. He saw her and stopped after opening the car door.

"What was it?" Blair asked.

"Nothing, really." He answered. "I'm going to Chuck's bar. I promised him."

"Why didn't you tell me?"

"Gosh, Blair. I tried." Nate faced her. "But whenever I did, something else has got your attention. A party. Another plot for school girls. I couldn't get in the way with your plans."

"Plans?" She raised her voice. "I planned that party for us to start over, why don't you get that?"

"I don't, really. I told you already that we will start over. You just can't trust me enough so you go on building this walls to cover for your insecurities."

"So, you're afraid to break that wall?"

"I know it would upset you, yes." Nate sighed. "Because that's the only way I could save you."

"Well, you know what, Nate Archibald," she pushed him out of the way. "I don't need any saving. I don't need you."

With that, she got in the limo and drove off.

*

"Where's Nate?" Chuck asked as Blair got out.

"I left him." She said. "I think we just broke up."

"Bass?"

"I need to escape. Can I stay here?"

They settled on the couch in front of the stage where dancers were stripping off.

"I know you don't want to talk about it but…"

"Relief. I feel relief." She said, looking at the dancers, chardonnay in her hands. "Hey Waldorf. Fill it up again."

"You already had three glasses ."

"Oh, fuck you." Blair took the bottle from the table and poured another for her. "I'm not even drunk yet."

"Nate is gonna kill me." Chuck sighed.

"Screw Nate!" She shouted. "Would you believe that? He told me I was being insecure! That these walls or something. He's afraid to upset me! Why should I be upset? I'm Blair Bass! I don't need any saving! I just... want…"

She stood up and and walked up the stage.

"Bass?" He whispered, looking mesmerized as she started stripping off her dress and began to show some moves. He got nailed with the sight of his best friend's girl friend.

"Thanks for bringing me here, Waldorf!" She shouted.

"Who's that girl?" A gay asked.

"I have no idea." Chuck answered, eyes still on Blair.

*

"Thanks for the lift home." Blair looked out the window. "Don't worry. Waldorf. I wasn't drunk. I am not, for that matter. It just felt so good to let it all out."

She faced him. "I wanted to cry then, when he told me I was insecure. It was like my father telling me my dress looks bad."

Chuck looked into her eyes. "You were… amazing back there."

She leaned closer. For the first time today, she had heard something good that made her feel good about herself. She heard something good about her that wasn't forced nor imposed and obligatory. He said it because it was true.

So she kissed him. A kiss she didn't even give Nate. She looked at him.

"Are you sure?" He asked.

She kissed him again. And it all happened at the back of his limo.


	2. Chapter 2

A/N: If you noticed, the genre says Romance/Family. And this story is basically CB's struggle with their parents (who don't even like their children that much)... I just wanted to figure out how CB will react if they were in each other's shoes...Or something like that in the latter parts. Well, let's just see^^.

P.S. I really forgot Nate's dad's name, so I'll keep calling him Captain.

* * *

**Of Blair Bass and Chuck Waldorf**

She's Blair Cornelia Bass, the only daughter of NY C's business tycoon Bart Bass, making her the ultimate princess of the Upper East Side.

He's Charles Bartholomew Waldorf, the infamous son of fashion designer Eleanor, and chef Harold Waldorf, known for his nickname Chuck and being a certified Casanova.

When these two come together, what would become of the Upper East Side?

* * *

**Chapter Two**

Nate had been day dreaming, playing with the ring he was supposed to give Blair last night. _Thank God. _ For once, he thought of gossip girl as a life saver. He was thinking of breaking up with her that night, at that moment, in front of their parents, and run away for a while until he can figure out what to do with his feelings for Serena, especially now that she's quite hot with Dan Humphrey.

"Oh, good." Captain appeared. "So, you're still sticking with the plan."

"Why are you doing this to me dad?"

"Because it's for your own good. Listen, marrying Blair would not only ensure you a good future."

"I know, you'd be ensured too."

Nate stood up and walked away, pounding the ring onto the table after going out the door.

*

"Blair!" Serena knocked for the sixteenth time on the door. "What is the matter with you? Did Nate do something to you?"

Dorota had contacted her mistress' best friend because she was worried that Blair wouldn't come out of the room. She came home late last night, looking tired, but it didn't seem like she was sad, she was actually happy. Then in the morning, they couldn't get her up for breakfast. Her room and locks that can only be opened from the inside.

"B, c'mon. You're scaring me..." Serena pleaded.

Somewhere in the corners of her boudoir, Princess Bass stared at her reflection in the mirror, vaguely hearing her best friend's voice outside her door. She looked normal, still beautiful, still Blair. But she didn't feel like it anymore. Somehow, she felt scared.

A ring came in from her phone. It was Nate.

**I'm sorry about last night.**

**Can we talk it over?**

She sighed as she put down the phone. Part of her wanted to reply. Part of her didn't. Not after what she and Chuck did, she betrayed Nate. She couldn't face him now. Especially after what Bart had said to her last night after she came home from Victrola.

"How's Nate?" He suddenly said after she entered the living room.

"I think we broke up." She shook her head.

"He left you?" Bart sounded as if it was expected. "I wonder why..."

"Dad..."

"Go to sleep. You don't look so good."

Finally taking final sigh, she stood up and walked to the door.

"I don't wanna do this B, But I'm busting your door!" Serena shouted.

There was no need for violence, Blair opened it. "Hi, S."

*

"Charles Bartholomew Waldorf. What is the meaning of this!?" Eleanor threw a mailed letter on Chuck's bed. He saw it was open.

"What? Is this some letter from Harold for your divorce?" He joked, she rolled her eyes, tapping her feet.

But it wasn't, it was his trust fund report. Eleanor had it checked yesterday and a large sum was practically missing.

"What did you do?"

"I bought the fucking club you didn't." He faced her. "I am going to earn back every dollar I've invested on it and you can do nothing to stop my business."

"Oh, I don't intend to, Charles."

"That's right, just stay out of it. This is my life, and I'm gonna have lots of fun. You can throw me out like what you've always wanted to do."

"I don't want to throw you out." She admitted. "Your dad would have a fit."

"Yeah," He smirked.

"But he won't tolerate this behavior either." Eleanor took hold of the door knob. "He's coming over. Just so you know, You are a Waldorf."

With that, she closed the door.

Chuck went back to bed. Harold will be coming over. This should've made him happy. It's been six months since he last saw him-not a good scene actually, after seeing his father kiss another man. He wouldn't be made a fool by anyone. The gossip girl blast had done much to him already.

_**Head's up Upper East Siders, we all know Chuck Waldorf-slick, rich, and a total Casanova. But who would've thought that he's dear old dad not only cooks great, but is also great doing guys? That's right fellas, keep your eyes open. We don't know who Waldorf junior might strike next.**_

"Chuck?" Nate tugged him, seeing that he was quite shocked.** "**Gossip girl is just probably lying. This couldn't be true."

He remained silent, clutching his phone. Every one around was looking at him. Others smiled, others laughed, others looked like if he had a disease or something.

"Chuck! Nate!" Blair was running down the steps. "Have you heard from gossip girl? God-"

"Shut up, Bass!" Chuck shouted.

"Chuck, don't take it out on her." Nate countered. "Besides, these are just rumors."

Blair looked at him, stunned. "It's not. It's true."

He gave her the eye, certainly, she knew better.

"_Oh, my God."_

"_He's dad's gay."_

"_Yeah, after all these years?"_

"_May be he's gay, too."_

He heard so many voices, it felt like his vision was spinning.

"Chuck." Blair held his arm.

"C'mon, man."

"Hey Waldorf!" Said a guy. "How about you do me instead?" Then every one laughed.

Chuck fired up, pushing Blair and Nate aside, heading for the object of his destruction.

"What? Let's get it on." Said the Chuck punched him. "What the-"

"Don't talk about my father that way!" He shouted as he took him by the collar. "You don't know him! He may be GAY, so what!? He is my father!"

He let him go. And the scared student ran away.

*

Serena had been staring at her for quite sometime now, But Blair hasn't said a word. How could she tell her about Chuck, about how good it made her feel? And Nate. Sure, Serena had done the classic "the boyfreind and the best friend", and she condemned her. Now that she's actually done the same thing, she's afraid Serena would leave her as well. She couldn't take it. She's been losing a lot lately. She can't afford to lose her best friend too.

"C'mon B. Really, you're starting to freak me out."

"if I... tell you," She began. "Promise you won't get mad." it was a statement.

"Yes. I promise."

Blair sighed. Serena's promises always puts her at ease.

"I don't really know where to begin. Nate, dad, Chuck-"

"Chuck?" Serena inquired. "How did he get in this?"

"You sound angry. You broke your promise."

"I was only asking B." She tapped her knee.

"You see, S. I think Nate and I broke up last night." Blair finally said.

"What, why?"

"He said he was afraid to hurt me. That I just build walls around to cover my insecurities. I know that already, he didn't have to push it."

"And?"

"I left him." She looked at her. "And I went to Chuck's bar."

Serena blinked, she had quite the thoughts. "You-"

"It felt great S." Blair smiled, for the fist time that day.

"Really?" Serena just nodded. "Well, Nate and Chuck are..."

"I know. It's like me doing what you did." She teased. "But really, there was something about Chuck Waldorf."

"What about Nate?"

"He wants to talk to me. Should I?"

Her best friend paused for a moment. Blair did had a different sparkle in her eyes when she mentioned Chuck. And she was acting all jelly-ish. Like someone who was lovestruck, acting all-weak and weird that didn't even seem real for Blair.

"You should." Serena said. "And don't do something you'll regret."

*

After an hour of walking, Nate stopped in front of a restaurant, clutching the ring he ought to give her. He found Blair, all ready and quite stunningly beautiful.

"Wow." He smiled as he took his seat. "You sure look blooming today."

"Really?" She twitched. "I'm a wild flower, you know."

Then came a silence between them. Nate just felt bad, he was still thinking that Blair believes he's going to marry her. He had his decisions now. And Marriage was important to her as any other thing. So he took out the ring.

"Oh, my. " She marveled at it. "Nate..."

"Blair, you know I love you." He sounded sorry, she saw it in him. "But you know-"

"I won't, Nate." She cut him off. "If you're asking me to marry you, I won't."

He looked surprised, surely, he didn't see this coming. "Why?"

"Because."

He looked at her, she bowed her head. He then smiled.

"I think you deserve better." they said at the same time. they both laughed.

"Really, Nate." Blair smiled.

"So, we're okay?"

"More than okay."

And they left the restaurant with joy in their hearts.


End file.
